反应 #1726680

反应方程式

3-hydroxyazetidine hydrochloride

triethylamine

ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate

sodium cyanide

→

1B

收率 90.0%

(3-Hydroxyazetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

收率 90.0%

溶剂

dichloromethane

water

methanol

methanol

反应条件

后处理

1. 1
   workup.ADDITIONwere added
2. 2
   其他The layers were separated
3. 3
   萃取the aqueous phase was extracted twice with dichloromethane (30 mL)
4. 4
   其他The combined organic layers were evaporated
5. 5
   workup.ADDITIONThe crude product was then treated with toluene (5 mL)
6. 6
   过滤filtered
7. 7
   洗涤washed with toluene (5 mL)
8. 8
   其他dried in vacuo

实验过程

To a clear solution of ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.40 g, 1.83 mmol) in dry methanol (5 mL) was added sodium cyanide (18 mg, 0.37 mmol). A solution of 3-hydroxyazetidine hydrochloride (0.45 g, 2.84 mmol) and triethylamine (0.40 mL, 2.84 mmol) in methanol (5 mL) was added at ambient temperature. After stirring for 20 min water (20 mL) and dichloromethane (30 mL) were added. The layers were separated and the aqueous phase was extracted twice with dichloromethane (30 mL). The combined organic layers were evaporated. The crude product was then treated with toluene (5 mL), filtered, washed with toluene (5 mL) and dried in vacuo. There was obtained 0.40 g (90%) of 1B as a solid. 1H NMR (400 MHz, DMSO-d6): δ 3.84 (dd, 1H), 4.31 (m, 2H), 4.56 (m, 1H), 4.79 (dd, 1H), 5.87 (d, 1H), 7.64 (m, 3H), 8.05 (d, 2H), MS (APCI+) m/z 246 [M+H]−.

来源